Ethyl benzoylacetate → N-(3-methoxyphenyl)-3-oxo-3-phenylpropanamide

HRID 1655020Notes

Reaction equation

HRID 1655020 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.[C:10]([CH2:18][C:19](OCC)=[O:20])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1.C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:19](=[O:20])[CH2:18][C:10](=[O:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 7170Ethyl benzoylacetateHCID 108243-Methoxyaniline

Product 1

HCID 699437N-(3-methoxyphenyl)-3-oxo-3-phenylpropanamide

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 7237O-XyleneSolvent

Procedure

A solution of m-anisidine (10 g), ethyl benzoylacetate (19 g) and pyridine (2 drops) in xylene (20 mL) was heated to reflux for 5 hr. The mixture was cooled to r.t. and concentrated. The residual material was subjected to chromatography (silica gel; hexane/EtOAc (4:1)), affording the title compound as an oil.

Workup

  1. temperatureto reflux for 5 hr
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-acfcda78abe34017b420033738ea57e6
Source dataset
uspto-grants-1995_04
Patent number
US05410054

Reaction notes

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